1,2-Dichloroethane → HCID 178522828, compound

HRID 1596522Notes

Reaction equation

HRID 1596522 reaction equation
F[C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][NH:5][C:6]([C@H:8]1[CH2:13][CH2:12][C@@H:11]([CH2:14][C:15]2[NH:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)=[O:7].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.C(N)C1C=CC=CC=1>CN(C=O)C>[CH2:4]([NH:5][C:6]([C@H:8]1[CH2:9][CH2:10][C@H:11]([CH2:14][C:15]2[NH:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:12][CH2:13]1)=[O:7])[C:3]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:2]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 7504BenzylamineHCID 181649HOAtHCID 178522833HCID 178522833, compound

Product 1

HCID 178522828HCID 178522828, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Example 8 was prepared by the following procedure. To a solution of trans-4-(1H-benzimidazol-2-ylmethyl)-cyclohexanecarboxylic acid (F) (444 mg, 1.72 mmol), EDC (328 mg, 1.72 mmol) and HOAt (234 mg, 1.72 mmol) in anhydrous DMF (4 mL) was added benzylamine (184 mg, 1.72 mmol). The resulting reaction mixture was stirred for 15 h. The reaction mixture was partitioned between saturated aqueous NaHCO3 and EtOAc and the organic layer washed 2× with water, and dried with MgSO4. Concentration gave trans-4-(1H-benzimidazol-2-ylmethyl)-cyclohexanecarboxylic acid benzylamide (400 mg, 67%) as a white solid. 1H NMR (400 MHz, CD3OD) δ 7.49 (br s, 2H), 7.30-7.17 (m, 7H), 4.34 (s, 2H), 2.78 (d, 2H), 2.21 (m, 1H), 1.84 (m, 5H), 1.55 (q, 2H), 1.16 (q, 2H); mass spectrum m/z 348 [(M+H)+; calcd for C22H26N3O: 348].

Workup

  1. customExample 8 was prepared by the following procedure
  2. customThe resulting reaction mixture
  3. customThe reaction mixture was partitioned between saturated aqueous NaHCO3 and EtOAc
  4. washthe organic layer washed 2× with water
  5. dry with materialdried with MgSO4
  6. concentrationConcentration

Sources & evidence

ORD record
ord-151c0dff14c348c48def6257e8d63b52
Source dataset
uspto-grants-2001_09
Patent number
US06291499B1

Reaction notes

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